Stars Hollow is a fictional Connecticut town that resembles Connecticut's beautiful Litchfield County. Litchfield County is in the Northwest corner of the state and borders New York and Massachusetts. It is known for it's antiques, it's historic inns and it's all-around charm. Sounds just like Stars Hollow. However, Stars Hollow's location is actually somewhere between the state's two best-known cities, Hartford and New Haven to accommodate Rory Gilmore's attendance at Yale University. This would make Stars Hollow more likely to be psychically in the New Haven-Naugatuck Valley (Middle of the state) area while still resembling Litchfield County villages. Here's a map of Connecticut to illustrate the point.